diff --git a/api/internal/builtins/HelmChartInflationGenerator.go b/api/internal/builtins/HelmChartInflationGenerator.go
index 40437a2155..be69576363 100644
--- a/api/internal/builtins/HelmChartInflationGenerator.go
+++ b/api/internal/builtins/HelmChartInflationGenerator.go
@@ -101,6 +101,14 @@ func (p *HelmChartInflationGeneratorPlugin) validateArgs() (err error) {
 		// the additional values filepaths must be relative to the kust root
 		p.AdditionalValuesFiles[i] = filepath.Join(p.h.Loader().Root(), file)
 	}
+	for key, file := range p.SetFile {
+		// use Load() to enforce root restrictions
+		if _, err := p.h.Loader().Load(file); err != nil {
+			return errors.WrapPrefixf(err, "could not load file '%s' specified in SetFile", file)
+		}
+		// the filepaths must be relative to the kust root
+		p.SetFile[key] = filepath.Join(p.h.Loader().Root(), file)
+	}
 
 	if err = p.errIfIllegalValuesMerge(); err != nil {
 		return err
diff --git a/api/krusty/helmchartinflationgenerator_test.go b/api/krusty/helmchartinflationgenerator_test.go
index daffa16a0a..52c446a2bd 100644
--- a/api/krusty/helmchartinflationgenerator_test.go
+++ b/api/krusty/helmchartinflationgenerator_test.go
@@ -436,6 +436,84 @@ metadata:
 `)
 }
 
+func TestHelmChartInflationGeneratorSetFile(t *testing.T) {
+	th := kusttest_test.MakeEnhancedHarnessWithTmpRoot(t)
+	defer th.Reset()
+	if err := th.ErrIfNoHelm(); err != nil {
+		t.Skip("skipping: " + err.Error())
+	}
+
+	copyValuesFilesTestChartsIntoHarness(t, th)
+
+	th.WriteF(filepath.Join(th.GetRoot(), "game.properties"), `
+enemy.types=aliens,monsters
+player.maximum-lives=5
+`)
+
+	th.WriteF(filepath.Join(th.GetRoot(), "user-interface.yaml"), `
+color:
+  good: purple
+  bad: yellow
+allow:
+  textmode: true
+`)
+
+	th.WriteK(th.GetRoot(), `
+helmCharts:
+  - name: test-chart
+    releaseName: test-chart
+    setFile:
+      config.game: game.properties
+      config.ui: user-interface.yaml
+`)
+
+	m := th.Run(th.GetRoot(), th.MakeOptionsPluginsEnabled())
+	asYaml, err := m.AsYaml()
+	require.NoError(t, err)
+	require.Equal(t, string(asYaml), `apiVersion: v1
+data:
+  game.properties: |2
+
+    enemy.types=aliens,monsters
+    player.maximum-lives=5
+  user-interface.yaml: |2
+
+    color:
+      good: purple
+      bad: yellow
+    allow:
+      textmode: true
+kind: ConfigMap
+metadata:
+  name: game-demo
+---
+apiVersion: apps/v1
+kind: Deployment
+metadata:
+  labels:
+    chart: test-1.0.0
+  name: my-deploy
+  namespace: default
+spec:
+  replicas: 1
+  selector:
+    matchLabels:
+      app: test
+  template:
+    spec:
+      containers:
+      - image: test-image:v1.0.0
+        imagePullPolicy: Always
+---
+apiVersion: apps/v1
+kind: Pod
+metadata:
+  annotations:
+    helm.sh/hook: test
+  name: test-chart
+`)
+}
+
 func TestHelmChartInflationGeneratorApiVersions(t *testing.T) {
 	th := kusttest_test.MakeEnhancedHarnessWithTmpRoot(t)
 	defer th.Reset()
diff --git a/api/krusty/testdata/helmcharts/test-chart/templates/configmap.yaml b/api/krusty/testdata/helmcharts/test-chart/templates/configmap.yaml
new file mode 100644
index 0000000000..c2be4708ed
--- /dev/null
+++ b/api/krusty/testdata/helmcharts/test-chart/templates/configmap.yaml
@@ -0,0 +1,11 @@
+---
+{{- if .Values.config }}
+apiVersion: v1
+kind: ConfigMap
+metadata:
+  name: game-demo
+data:
+  # file-like keys
+  game.properties: {{ .Values.config.game | toYaml | indent 2 }}
+  user-interface.yaml: {{ .Values.config.ui | toYaml | indent 2 }}
+{{- end }}
\ No newline at end of file
diff --git a/api/types/helmchartargs.go b/api/types/helmchartargs.go
index 15ea7178fb..7c948b4844 100644
--- a/api/types/helmchartargs.go
+++ b/api/types/helmchartargs.go
@@ -63,6 +63,11 @@ type HelmChart struct {
 	// addition to either the default values file or the values specified in ValuesFile.
 	AdditionalValuesFiles []string `json:"additionalValuesFiles,omitempty" yaml:"additionalValuesFiles,omitempty"`
 
+	// SetFile holds value mappings where the value is specified in a file.
+	// This allows setting values from respective files. The file's content
+	// will become the value's content.
+	SetFile map[string]string `json:"setFile,omitempty" yaml:"setFile,omitempty"`
+
 	// ValuesFile is a local file path to a values file to use _instead of_
 	// the default values that accompanied the chart.
 	// The default values are in '{ChartHome}/{Name}/values.yaml'.
@@ -168,6 +173,9 @@ func (h HelmChart) AsHelmArgs(absChartHome string) []string {
 	for _, valuesFile := range h.AdditionalValuesFiles {
 		args = append(args, "-f", valuesFile)
 	}
+	for key, file := range h.SetFile {
+		args = append(args, "--set-file", key+"="+file)
+	}
 
 	for _, apiVer := range h.ApiVersions {
 		args = append(args, "--api-versions", apiVer)
diff --git a/plugin/builtin/helmchartinflationgenerator/HelmChartInflationGenerator.go b/plugin/builtin/helmchartinflationgenerator/HelmChartInflationGenerator.go
index 01adb29f5b..3f8d832365 100644
--- a/plugin/builtin/helmchartinflationgenerator/HelmChartInflationGenerator.go
+++ b/plugin/builtin/helmchartinflationgenerator/HelmChartInflationGenerator.go
@@ -107,6 +107,14 @@ func (p *plugin) validateArgs() (err error) {
 		// the additional values filepaths must be relative to the kust root
 		p.AdditionalValuesFiles[i] = filepath.Join(p.h.Loader().Root(), file)
 	}
+	for key, file := range p.SetFile {
+		// use Load() to enforce root restrictions
+		if _, err := p.h.Loader().Load(file); err != nil {
+			return errors.WrapPrefixf(err, "could not load file '%s' specified in SetFile", file)
+		}
+		// the filepaths must be relative to the kust root
+		p.SetFile[key] = filepath.Join(p.h.Loader().Root(), file)
+	}
 
 	if err = p.errIfIllegalValuesMerge(); err != nil {
 		return err
diff --git a/plugin/builtin/helmchartinflationgenerator/HelmChartInflationGenerator_test.go b/plugin/builtin/helmchartinflationgenerator/HelmChartInflationGenerator_test.go
index d75b44d1dc..d4cfb0e9c0 100644
--- a/plugin/builtin/helmchartinflationgenerator/HelmChartInflationGenerator_test.go
+++ b/plugin/builtin/helmchartinflationgenerator/HelmChartInflationGenerator_test.go
@@ -430,6 +430,62 @@ valuesFile: myValues.yaml
 		))
 }
 
+func TestHelmChartInflationGeneratorSetFile(t *testing.T) {
+	th := kusttest_test.MakeEnhancedHarnessWithTmpRoot(t).
+		PrepBuiltin("HelmChartInflationGenerator")
+	defer th.Reset()
+	if err := th.ErrIfNoHelm(); err != nil {
+		t.Skip("skipping: " + err.Error())
+	}
+
+	copyTestChartsIntoHarness(t, th)
+
+	th.WriteF(filepath.Join(th.GetRoot(), "game.properties"), `
+enemy.types=aliens,monsters
+player.maximum-lives=5
+`)
+
+	th.WriteF(filepath.Join(th.GetRoot(), "user-interface.yaml"), `
+color:
+  good: purple
+  bad: yellow
+allow:
+  textmode: true
+`)
+
+	rm := th.LoadAndRunGenerator(`
+apiVersion: builtin
+kind: HelmChartInflationGenerator
+metadata:
+  name: test-chart
+name: test-chart
+releaseName: test-chart
+chartHome: ./charts
+setFile:
+  config.game: game.properties
+  config.ui: user-interface.yaml
+`)
+
+	th.AssertActualEqualsExpected(rm, `
+apiVersion: v1
+data:
+  game.properties: |2
+
+    enemy.types=aliens,monsters
+    player.maximum-lives=5
+  user-interface.yaml: |2
+
+    color:
+      good: purple
+      bad: yellow
+    allow:
+      textmode: true
+kind: ConfigMap
+metadata:
+  name: bar
+`)
+}
+
 func TestHelmChartInflationGeneratorWithInLineReplace(t *testing.T) {
 	th := kusttest_test.MakeEnhancedHarnessWithTmpRoot(t).
 		PrepBuiltin("HelmChartInflationGenerator")
diff --git a/plugin/builtin/helmchartinflationgenerator/testdata/charts/test-chart/README.md b/plugin/builtin/helmchartinflationgenerator/testdata/charts/test-chart/README.md
new file mode 100644
index 0000000000..3b1383634c
--- /dev/null
+++ b/plugin/builtin/helmchartinflationgenerator/testdata/charts/test-chart/README.md
@@ -0,0 +1 @@
+This is a simple test chart.
\ No newline at end of file
diff --git a/plugin/builtin/helmchartinflationgenerator/testdata/charts/test-chart/templates/configmap.yaml b/plugin/builtin/helmchartinflationgenerator/testdata/charts/test-chart/templates/configmap.yaml
index b7c8ef451a..733229214d 100644
--- a/plugin/builtin/helmchartinflationgenerator/testdata/charts/test-chart/templates/configmap.yaml
+++ b/plugin/builtin/helmchartinflationgenerator/testdata/charts/test-chart/templates/configmap.yaml
@@ -2,3 +2,9 @@ apiVersion: v1
 kind: ConfigMap
 metadata:
   name: {{ .Values.foo }}
+{{- if .Values.config }}
+data:
+  # file-like keys
+  game.properties: {{ .Values.config.game | toYaml | indent 2 }}
+  user-interface.yaml: {{ .Values.config.ui | toYaml | indent 2 }}
+{{- end }}